Grouping text to drawing object

Anyone know how to group text to a drawing object?
It seems easy until you try it…

I’ve drawn a picture of a truck and want to add text to the side of the truck.

All I’ve found is an option to break the text up into drawing objects, but even this doesn’t enable the “group” option on the tool menu, which remains greyed-out.

I’m sure there’s a trick to this - just can’t find it.
Any suggestions?

Fixed - kind of…

Looks like you have to select “Break text apart” multiple times until the Group option is no longer greyed out.

…but this does leave another problem.

I was hoping to be able to edit the drawing of the truck at a later stage, changing the color and the text. However, when you group text using the “break text appart” option, the text is no longer editable. It looks like you have to ungroup the drawing object and text. Group the broken apart text and then delete it and replace it with new text, break that apart and then group everything back together again. There must be an easier way…